Shikimic Acid


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shikimic acid

[shə′kim·ik ′as·əd]
(biochemistry)
C7H10O5 A crystalline acid that is a plant constituent, and an intermediate in the biochemical pathway from phosphoenolpyruvic acid to tyrosine.

Shikimic Acid

 

the most important intermediate product of metabolism in microorganisms and higher plants; colorless crystals, with a melting point of 184°C and good solubility in water.

The biochemical role of shikimic acid was elucidated in 1955–58 by the American microbiologist B. Davis while working with mutants of Bacillus coli. The formation of the acid is related to carbohydrate metabolism; its closest precursor is 7-phosphate-3-deoxyarabinoheptulose. Shikimic acid takes part in the biosynthesis of aromatic acids, including the amino acids phenylalanine, tyrosine, and tryptophan; phenol compounds, including phenol alkaloids; coumarins; lignin; and flavonoid pigments and other secondary metabolites.

REFERENCES

Zaprometov, M. N. Osnovy biokhimii fenol’nykh soedinenii. Moscow, 1974.
Biokhimiia rastenii. Moscow, 1968. (Translated from English.)
References in periodicals archive ?
An interesting Cyprus connection is that Shikimic Acid is to be found in two of our native plants, Pistacia lentiscus, the mastic tree, and Opuntia ficus-indica, the prickly pear.
Compound rt (min) PDA rt (min) QqQ Hydroxybenzoic acids (1) Shikimic acid 1.50 2.35 (2) Protocatechuic acid 5.99 6.80 (3) 4-Hydroxybenzoic acid 8.05 8.82 (4) Vanillic acid 9.04 9.82 (5) Syringic acid 9.31 10.06 Hydroxycinnamic acids (6) Quinic acid 1.51 2.28 (7) Chlorogenic acid 7.51 8.30 (8) Caffeic acid 9.09 9.85 (9) Coumaric acid 11.07 11.79 (10) Sinapic acid 11.65 12.36 (11) Ferulic acid 11.73 12.43 (12) 4,5-Dicaffeoylquinic 11.75 12.45 acid Xanthones (13) Mangiferin 8.83 9.62 Flavonols (14) Rutin 10.86 11.62 (15) Isoquercitrin 11.34 12.10 (16) Quercetin 15.25 16.01 (17) Kaempferol 17.16 17.89 Flavanones (18) Naringin 12.07 12.82 (19) Naringenin 16.86 17.53 Flavones (20) Linarin 12.43 13.22 (21) Luteolin 15.08 15.85 (22) Acacetin 16.08 17.03 (23) Apigenin 16.68 17.38 [[lambda].sub No.
Biosynthetically, the B-ring and linking three-carbon chain (C6-C3) are the phenylpropanoid skeleton that is derived from the shikimic acid pathway, while the other C-6 (A-ring) is an acetate pathway origin that bears the three hydroxyl groups spaced at meta positions from each other within the benzene ring.
Gao, "Antibacterial activity of shikimic acid from pine needles of Cedrus deodara against Staphylococcus aureus through damage to cell membrane," International Journal of Molecular Sciences, vol.
We have come up with new indigenous processes of shikimic acid production for large- scale validation.
Rap biosynthesis in media enriched with different concentrations of shikimic acid and CaP.
Shikimic acid is a white crystalline cyclitol, which is a precursor material for industrial synthesis of the important drug, oseltamivir phosphate (Tamiflu), which is an effective drug againstthe H5N1 influenza virus [1], especially if administered early.
It covers chirality, topology, and asymmetric synthesis; asymmetric synthesis; sugars; amino acids, peptides, and proteins; nucleosides, nucleotides, and nucleic acids; polyketides; terpenes; shikimic acid derivatives; and alkaloids.
These compounds are allelochemicals which are usually the secondary or waste products of main plants methabolic pathways specially shikimic acid and acetate pathways [21].
coli of shikimic acid, the starter molecule for production of oseltamivir, marketed as Tamiflu, for treatment of severe influenza (Johansson et al., 2005).